2-Cyano-6-methoxybenzothiazole Struktur

2-Cyano-6-methoxybenzothiazole

Bezeichnung:2-Cyano-6-methoxybenzothiazole

CAS-Nr943-03-3

Englisch Name:2-Cyano-6-methoxybenzothiazole

CBNumberCB8467670

SummenformelC9H6N2OS

Molgewicht190.22

MOL-Datei943-03-3.mol

2-Cyano-6-methoxybenzothiazole physikalisch-chemischer Eigenschaften

Schmelzpunkt	129-131 °C (lit.)
Siedepunkt	334.9±34.0 °C(Predicted)
Dichte	1.2938 (rough estimate)
Brechungsindex	1.6800 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	chloroform: soluble5%, clear, colorless to faintly yellow
Aggregatzustand	Crystalline Powder
pka	-1.49±0.10(Predicted)
Farbe	Off-white to light yellow
InChI	InChI=1S/C9H6N2OS/c1-12-6-2-3-7-8(4-6)13-9(5-10)11-7/h2-4H,1H3
InChIKey	DEWDWBYQOFXKIH-UHFFFAOYSA-N
SMILES	S1C2=CC(OC)=CC=C2N=C1C#N
CAS Datenbank	943-03-3(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	20/21/22-36/37/38
S-Sätze:	26-36-36/37
RIDADR	3439
WGK Germany	3
HS Code	29341000

Gefahreninformationscode (GHS)

2-Cyano-6-methoxybenzothiazole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Chemische Eigenschaften
off-white to light yellow crystalline powder
Verwenden
2-Cyano-6-methoxybenzothiazole has been used in the synthesis of:
- firefly luciferin via condensation with cysteine
- luciferin β-glycosides, substrates for novel ultrasensitive enzyme assays
Verwenden
Luciferin intermediate.
Synthese
Typical routes to 2-cyano-6-methoxybenzothiazole include the classical Rosenmund-von Braun and Sandmeyer reactions. These methods proceed with low atom economy and require toxic reagents such as KCN, NaCN, Zn(CN)2, or TMSCN, which are also challenging to handle in a large-scale synthesis. Shahmoradi et al. introduced a Cu-catalyzed cyanation of 2-iodo-6-methoxybenzothiazole to synthesize 2-cyano-6-methoxybenzothiazole. K4[Fe(CN)6] was applied as a source of cyanide, and CuI in the presence of N, N N′, N′-tetramethylethylenediamine (TMEDA) was used as part of the catalyst system. 2-Amino-6-methoxybenzothiazole as a starting material was synthesized from p-anisidine as shown below and subsequently converted into 2-iodo-6-methoxybenzothiazole using a simple and efficient one-pot sequential diazotization-iodination method. The one-pot cyanation of 2-iodo-6-methoxybenzothiazole to 2-cyano-6-methoxybenzothiazole was achieved using 0.25 mmol of K4[Fe(CN)6], 0.25 mmol of CuI and 3 mmol of TMEDA in acetonitrile at 160°C. In addition, 1 mmol of mystril trimethyl bromide (MTMAB) was used as a phase transfer agent. The presence of a phase-transfer catalyst is essential for a successful cyanation reaction. Under these conditions, 2-cyano-6-methoxybenzothiazole was produced in a 90% yield[1].
Einzelnachweise
[1] Ghasem Shahmoradi, S. Amani. “Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor.” Heterocyclic Communications 24 1 (2018): 255–258.

2-Cyano-6-methoxybenzothiazole Upstream-Materialien And Downstream Produkte

2-Cyano-6-methoxybenzothiazole Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

943-03-3, 2-Cyano-6-methoxybenzothiazole Verwandte Suche:

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